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US4273574A - 2-[3-(4-Chlorophenoxy)propylthio]-5-(1,3,3-trimethylureido)-1,3,4-thiadiazole and use as a post-emergent herbicide - Google Patents

2-[3-(4-Chlorophenoxy)propylthio]-5-(1,3,3-trimethylureido)-1,3,4-thiadiazole and use as a post-emergent herbicide Download PDF

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Publication number
US4273574A
US4273574A US06/178,240 US17824080A US4273574A US 4273574 A US4273574 A US 4273574A US 17824080 A US17824080 A US 17824080A US 4273574 A US4273574 A US 4273574A
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Prior art keywords
herbicide
post
thiadiazole
chlorophenoxy
trimethylureido
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Expired - Lifetime
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US06/178,240
Inventor
Joel L. Kirkpatrick
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Chevron USA Inc
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Gulf Oil Corp
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Priority to US06/178,240 priority Critical patent/US4273574A/en
Assigned to GULF OIL CORPORATION, A CORP. OF PA. reassignment GULF OIL CORPORATION, A CORP. OF PA. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: KIRKPATRICK JOEL L.
Application granted granted Critical
Publication of US4273574A publication Critical patent/US4273574A/en
Assigned to CHEVRON RESEARCH COMPANY reassignment CHEVRON RESEARCH COMPANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: CHEVRON U.S.A. INC.
Assigned to CHEVRON U.S.A. INC. reassignment CHEVRON U.S.A. INC. MERGER (SEE DOCUMENT FOR DETAILS). Assignors: GULF OIL CORPORATION
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • novel herbicide may be prepared from commercially available chemical intermediates by means of the reaction scheme outlined below. ##STR3##
  • novel herbicide is particularly effective when used post-emergently against weeds in fields of peanuts, rice and grain sorghum. Greenhouse tests are described below to illustrate selective control of unwanted vegetation.
  • aqueous dispersion of the herbicide compound was prepared by combining 0.4 gram of the compound with about 4 ml. of a solvent-emulsifier mixture (3 parts of a commercial polyoxyethylated vegetable oil emulsifier, one part xylene, one part kerosene) and then adding water, with stirring, to a final volume of 40 ml.
  • a solvent-emulsifier mixture (3 parts of a commercial polyoxyethylated vegetable oil emulsifier, one part xylene, one part kerosene
  • the species of plants on which the compound was tested were planted in disposable plastic pots in a greenhouse. Ten to eighteen days after emergence of the plants, three pots of each species were sprayed at each application rate with an aqueous dispersion of the active compound prepared as described above, at a rate of 1 lb. of active compound per acre and at a spray volume of 40 gal. per acre. Approximately one week after the spray application the plants were observed and phytotoxicity was rated according to the following schedule.
  • the herbicidal compound is effective at lower application rates than 1 lb. per acre.
  • the herbicide was applied to 12 species at lower rates, according to the procedure described above.
  • the herbicidal injury was scored on a schedule of zero (no injury) to 10 (complete kill). The results are tabulated below.
  • test results disclosed above serve to illustrate the selectivity and efficacy of the novel herbicide. These data will enable a worker in the art to make a selection of application rates and form a judgment as to whether the herbicide is suitable for a particular crop and weed problem. It may be seen, for example, that application rates as low as 1 oz. per acre are sufficient to control certain specific weeds, whereas as much as 1 lb. per acre may be necessary to combat other species. It may be preferable to use the herbicide at a low rate in combination with another efficient herbicide of different selectivity in some situations. It will be understood that higher rates of application may be required to combat vegetation which has become toughened by growth under adverse climatic conditions.
  • formulations of the herbicide desirably contain from 0.1 percent to 95 percent by weight of the active compound of formula (II) and from 0.1 to 75 percent by weight of a carrier or surfactant, the more dilute formulations being usually in the form of sprays, ready for application to plants.
  • the more concentrated formulations are most conveniently prepared as emulsifiable concentrates or wettable powders which may be diluted with a relatively large amount of water to make spray mixtures.
  • Wettable powders comprise intimate, finely divided mixtures of the herbicide, inert solid carriers and surface active agents.
  • the inert solid carrier is usually chosen from among the attapulgite clays, the kaolin clays, the montmorillonite clays, the diatomaceous earths, finely divided silica and purified silicates.
  • Effective surfactants which have wetting, penetrating and dispersing ability are usually present in a wettable powder formulation in proportions of from 0.5 to about 10 percent by weight.
  • the surface active agents commonly used for this purpose are the sulfonated lignins, naphthalenesulfonates and condensed naphthalenesulfonates, alkylbenzenesulfonates, alkyl sulfates and non-ionic surfactants such as products of condensation of ethylene oxide with alkylphenols.
  • Emulsifiable concentrates of the herbicide comprise in each instance, a solution of herbicide compound in a liquid carrier which is a mixture of water-immiscible solvent and surfactants, including emulsifiers.
  • a liquid carrier which is a mixture of water-immiscible solvent and surfactants, including emulsifiers.
  • Useful solvents include aromatic hydrocarbon solvents such as the xylenes, alkylnaphthalenes, petroleum distillates, terpene solvents, ether-alcohols and organic ester solvents.
  • Suitable emulsifiers, dispersing and wetting agents may be selected from the same classes of products which are employed in formulating wettable powders.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A novel compound having the structural formula ##STR1## is disclosed, which is particularly useful as a post-emergent herbicide for combating unwanted vegetation in the presence of peanuts, rice and grain sorghum.

Description

DESCRIPTION OF THE INVENTION
Highly active thiadiazoleurea herbicides of little or no selectivity are disclosed, for example, in U.S. Pat. No. 4,086,077. Other compounds with selectivity of a narrow, specific type which may be used in one or two crops are very desirable and have been disclosed, for example, in U.S. Pat. No. 4,141,717. Herbicides with specific selectivity are preferred because they give more efficient control of unwanted vegetation. However, there is a scarcity of herbicides of this type. For the most part, the selective herbicides in commercial use are useful in a larger number of crops but are not effective against a large number of weed species.
Briefly, I have discovered a novel compound having the structural formula ##STR2## which is effective against many of the common pestiferous weed species and is particularly useful for post-emergent control of unwanted vegetation in peanuts, rice and grain sorghum.
The novel herbicide may be prepared from commercially available chemical intermediates by means of the reaction scheme outlined below. ##STR3##
The method is illustrated by means of the following specific procedures.
To a mixture of 993.4 g. (6.75 moles) of 2-mercapto-5-methylamino-1,3,4-thiadiazole, 540 g. of 50% NaOH (6.75 mols), 3150 ml. of isopropyl alcohol and 1650 ml. of water is added 1258 g. (6.13 mols) of 3-(4'-chlorophenoxy) propyl chloride, and the resultant mixture is heated to reflux for 2 hours. Upon cooling to room temperature the contents of the reaction vessel are a solid mass. This is broken up, slurried with 3600 ml. of water, filtered and washed with water to give 1689 g. (91.3% yield) of the product, Compound (I) melting at 102.5°-104.5° C.
A solution of 452.8 g. (1.5 mols) of 2-(4'Chlorophenoxypropylthio)-5-methylamino-1,3,4-thiadiazole (m.p. 102°-5° C.) in 2250 ml. of toluene is treated with anhydrous HCl until the mixture becomes a very thick slurry. During this time the temperature of the mixture rises to about 40° C. An additional 500 ml. of toluene is added, the slurry is heated to 105° C. and, with stirring, a stream of phosgene is passed through the mixture. A total of 98.9 g. of phosgene is added over a 3 hour period, during which time the slurry thins and finally becomes a clear yellow solution. After cooling in an ice bath to 20° C. while sweeping nitrogen through the system, sufficient 40% aqueous dimethylamine (about 620 ml.) is added slowly, while keeping the temperature below 30° C., to bring the mixture to pH 9. The solution is washed successively with 350 ml. portions of water, 10% HCl and water again, then with two 500 ml. portions of 15% NaOH, dried over anhydrous sodium sulphate and the toluene is removed under vacuum, giving 551.5 g. of product (91.2% yield) as a heavy oil. (Compound II).
SELECTIVELY COMBATTING UNWANTED VEGETATION
The novel herbicide is particularly effective when used post-emergently against weeds in fields of peanuts, rice and grain sorghum. Greenhouse tests are described below to illustrate selective control of unwanted vegetation.
PROCEDURE
An aqueous dispersion of the herbicide compound was prepared by combining 0.4 gram of the compound with about 4 ml. of a solvent-emulsifier mixture (3 parts of a commercial polyoxyethylated vegetable oil emulsifier, one part xylene, one part kerosene) and then adding water, with stirring, to a final volume of 40 ml.
The species of plants on which the compound was tested were planted in disposable plastic pots in a greenhouse. Ten to eighteen days after emergence of the plants, three pots of each species were sprayed at each application rate with an aqueous dispersion of the active compound prepared as described above, at a rate of 1 lb. of active compound per acre and at a spray volume of 40 gal. per acre. Approximately one week after the spray application the plants were observed and phytotoxicity was rated according to the following schedule.
0--no control or injury
1--1 to 25 percent control or injury
2--26 to 75 percent control or injury
3--76 to 99 percent control or injury
4--complete control or kill
Results of tests of the herbicide on 24 species are tabulated below.
              TABLE 1                                                     
______________________________________                                    
Results of Use of 2-[3-(4-Chlorophenoxy)propylthio]-5-                    
(1,3,3-trimethylureido)-1,3,4-thiadiazole                                 
Post-Emergently at 1 lb. per Acre                                         
Plant Species              Rating                                         
______________________________________                                    
Cocklebur (Xanthium pensylvanicum)                                        
                           4                                              
Lambsquarters (Chenopodium album)                                         
                           4                                              
Morning Glory (Ipomea purpurea)                                           
                           4                                              
Pigweed (Amaranthus retroflexus)                                          
                           4                                              
Wild Buckwheat (Polygonum convolvulus)                                    
                           4                                              
Wild Mustard (Brassica kaber)                                             
                           4                                              
Barnyard Grass (Echinochloa crusgalli)                                    
                           2                                              
Crabgrass (Digitaria sanguinalis)                                         
                           2                                              
Downy Brome (Bromus tectorum)                                             
                           3                                              
Giant Foxtail (Setaria faberii)                                           
                           3                                              
Green Foxtail (Setaria viridis)                                           
                           4                                              
Nutsedge (Cyperus esculentus)                                             
                           1                                              
Shattercane (Sorghum bicolor)                                             
                           2                                              
Wild Oats (Avena fatua)    4                                              
Alfalfa (Medicago sativa)  4                                              
Cotton (Gossypium herbaceum)                                              
                           4                                              
Peanut (Arachis hypogaea)  2                                              
Soybean (Soja max)         4                                              
Sugar Beet (Beta vulgaris) 4                                              
Tomato (Lycopersicum esculentum)                                          
                           4                                              
Corn (Zea mays)            3                                              
Grain Sorghum (Sorghum vulgare)                                           
                           2                                              
Rice (Oryza sativa)        2                                              
Wheat (Triticum aestivum)  4                                              
______________________________________
The herbicidal compound is effective at lower application rates than 1 lb. per acre. The herbicide was applied to 12 species at lower rates, according to the procedure described above. The herbicidal injury was scored on a schedule of zero (no injury) to 10 (complete kill). The results are tabulated below.
              TABLE 2                                                     
______________________________________                                    
RESULTS OF POST-EMERGENT USE OF THE HERBICIDE                             
AT LOW APPLICATION RATES                                                  
                     Score   Score   Score                                
                     at 1/2  at 1/8  at 1/16                              
Plant Species        lb/A.   lb/A.   lb/A.                                
______________________________________                                    
Pigweed (Amaranthus retroflexus)                                          
                     10      10      10                                   
Alfalfa (Medicago sativa)                                                 
                     10      6       4                                    
Tomato (Lycopersicum esculentum)                                          
                     10      10      6                                    
Cotton (Gossypium herbaceum)                                              
                     10      10      10                                   
Soybean (Soja max)   10      10      10                                   
Peanut (Arachis hypogaea)                                                 
                     2       2       1                                    
Yellow Foxtail (Setaria glauca)                                           
                     2       0       0                                    
Smartweed (Polygonum pensylvanicum)                                       
                     10      10      10                                   
Velvet Leaf (Abutilon cheophrasti)                                        
                     10      10      10                                   
Jimson Weed (Datura stramonium)                                           
                     10      10      10                                   
Morning Glory (Ipomea purpurea)                                           
                     10      10      9                                    
Cocklebur (Xanthium pensylvanicum)                                        
                     10      10      10                                   
______________________________________
The test results disclosed above serve to illustrate the selectivity and efficacy of the novel herbicide. These data will enable a worker in the art to make a selection of application rates and form a judgment as to whether the herbicide is suitable for a particular crop and weed problem. It may be seen, for example, that application rates as low as 1 oz. per acre are sufficient to control certain specific weeds, whereas as much as 1 lb. per acre may be necessary to combat other species. It may be preferable to use the herbicide at a low rate in combination with another efficient herbicide of different selectivity in some situations. It will be understood that higher rates of application may be required to combat vegetation which has become toughened by growth under adverse climatic conditions.
In general, formulations of the herbicide desirably contain from 0.1 percent to 95 percent by weight of the active compound of formula (II) and from 0.1 to 75 percent by weight of a carrier or surfactant, the more dilute formulations being usually in the form of sprays, ready for application to plants. The more concentrated formulations are most conveniently prepared as emulsifiable concentrates or wettable powders which may be diluted with a relatively large amount of water to make spray mixtures.
Wettable powders comprise intimate, finely divided mixtures of the herbicide, inert solid carriers and surface active agents. The inert solid carrier is usually chosen from among the attapulgite clays, the kaolin clays, the montmorillonite clays, the diatomaceous earths, finely divided silica and purified silicates. Effective surfactants, which have wetting, penetrating and dispersing ability are usually present in a wettable powder formulation in proportions of from 0.5 to about 10 percent by weight. Among the surface active agents commonly used for this purpose are the sulfonated lignins, naphthalenesulfonates and condensed naphthalenesulfonates, alkylbenzenesulfonates, alkyl sulfates and non-ionic surfactants such as products of condensation of ethylene oxide with alkylphenols.
Emulsifiable concentrates of the herbicide comprise in each instance, a solution of herbicide compound in a liquid carrier which is a mixture of water-immiscible solvent and surfactants, including emulsifiers. Useful solvents include aromatic hydrocarbon solvents such as the xylenes, alkylnaphthalenes, petroleum distillates, terpene solvents, ether-alcohols and organic ester solvents. Suitable emulsifiers, dispersing and wetting agents may be selected from the same classes of products which are employed in formulating wettable powders.

Claims (6)

I claim:
1. 2-[3-(4-Chlorophenoxy)propylthio]-5-(1,3,3-trimethylureido)-1,3,4-thiadiazole.
2. A herbicidal formulation which comprises from 0.1 percent to 95 percent by weight of the compound of claim 1 in combination with from 0.1 to 75 percent by weight of a carrier or surface active agent.
3. The method of selectively combating unwanted vegetation which comprises applying to said vegetation an effective amount of the compound of claim 1.
4. The method of claim 3 in which unwanted vegetation is combated in the presence of a growing crop of peanuts.
5. The method of claim 3 in which unwanted vegetation is combated in the presence of a growing crop of rice.
6. The method of claim 3 in which unwanted vegetation is combated in the presence of a growing crop of grain sorghum.
US06/178,240 1980-08-14 1980-08-14 2-[3-(4-Chlorophenoxy)propylthio]-5-(1,3,3-trimethylureido)-1,3,4-thiadiazole and use as a post-emergent herbicide Expired - Lifetime US4273574A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4589910A (en) * 1982-06-19 1986-05-20 Basf Aktiengesellschaft Novel 4'(benzisothiazo-5-yloxy)-phenylurea derivatives, their preparation and their use as herbicides
US4642132A (en) * 1982-01-22 1987-02-10 Basf Aktiengesellschaft Aminothiadiazoles and their use for controlling undesirable plant growth
WO2012030681A1 (en) * 2010-08-31 2012-03-08 Dow Agrosciences Llc Pesticidal compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4073793A (en) * 1976-01-16 1978-02-14 Schering Aktiengesellschaft 5-Alkylureido-1,3,4-thiadiazol-2-yl-sulfonyl-acetic acid derivatives
US4086077A (en) * 1970-04-17 1978-04-25 Gulf Research & Development Company Combating unwanted vegetation with 1,3,4-thiadiazolylureas
US4141717A (en) * 1976-06-30 1979-02-27 Gulf Oil Corporation Combating weeds in soybeans
US4233057A (en) * 1979-05-14 1980-11-11 Ppg Industries, Inc. 3-[5-(1-Phenoxy-alkyl, -alkynyl, -alkenyl, or haloalkyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinones

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4086077A (en) * 1970-04-17 1978-04-25 Gulf Research & Development Company Combating unwanted vegetation with 1,3,4-thiadiazolylureas
US4073793A (en) * 1976-01-16 1978-02-14 Schering Aktiengesellschaft 5-Alkylureido-1,3,4-thiadiazol-2-yl-sulfonyl-acetic acid derivatives
US4141717A (en) * 1976-06-30 1979-02-27 Gulf Oil Corporation Combating weeds in soybeans
US4233057A (en) * 1979-05-14 1980-11-11 Ppg Industries, Inc. 3-[5-(1-Phenoxy-alkyl, -alkynyl, -alkenyl, or haloalkyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinones

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4642132A (en) * 1982-01-22 1987-02-10 Basf Aktiengesellschaft Aminothiadiazoles and their use for controlling undesirable plant growth
US4589910A (en) * 1982-06-19 1986-05-20 Basf Aktiengesellschaft Novel 4'(benzisothiazo-5-yloxy)-phenylurea derivatives, their preparation and their use as herbicides
WO2012030681A1 (en) * 2010-08-31 2012-03-08 Dow Agrosciences Llc Pesticidal compositions
JP2013538216A (en) * 2010-08-31 2013-10-10 ダウ アグロサイエンシィズ エルエルシー Agrochemical composition
AP3445A (en) * 2010-08-31 2015-10-31 Dow Agrosciences Llc Pesticidal compositions
RU2606641C2 (en) * 2010-08-31 2017-01-10 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Pesticide compositions

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